Triphenylphosphine → 3-Benzofurancarboxylic acid, methyl ester

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 2.43 g (9.45 mmol) of 3-(2-Bromo-phenoxy) acrylic acid methyl ester, prepared as in Intermediate 17, 1.98 g (7.56 mmol, 0.8 equiv) of triphenylphosphine, 794 mg (9.45 mmol, 1.0 equiv) of NaHCO3, and 848 mg (3.78 mmol, 0.4 equiv) of palladium (II) acetate in 25 mL of DMF is heated to 110° C. for 16 h. After cooling to RT, the reaction mixture is diluted with 100 mL of Et2O and extracted with H2O (1×100 mL), dried (MgSO4), and the solvents removed in vacuo. Purification of the crude material by silica gel flash column chromatography afforded 650 mg of the title compound as a yellow oil: 1H NMR (CDCl3, 300 MHz) δ8.22 (s, 1H), 8.06 (m, 1H), 7.55 (m, 1H), 7.37 (m, 2H), 3.95 (s, 3H); Rf =0.50 in hexane/EtOAc 5/1.

Provenance & Evidence